Jay DeMarcus Reveals Keith Urban Almost Recorded Rascal Flatts’ Iconic Hit, ‘What Hurts The Most’

When Rascal Flatts recorded “What Hurts the Most” in 2006, they were searching for the perfect song to kick off a new era. From the first listen, it was a stand-out for them, but according to Jay DeMarcus, the band almost missed out on what would become one of the biggest hits of their career, as Keith Urban was in line to record the song first.

Sitting down with Audacy’s Katie Neal, DeMarcus explained that the song was brought to the band by producer Dann Huff as they began shaping what would become their iconic Me and My Gang album. It was first recorded by Mark Wills in 2003, but Huff was determined to give this track a chance to come to life in a new way. So after Keith Urban ultimately passed on it, the award-winning producer believed it was a perfect fit for Rascal Flatts.

“I think it was one of those moments we were looking for a big song to release first,” DeMarcus shared. “[Huff] said, ‘Look, this has been cut before.’ Mark Wills had cut it. He said, ‘But I’ve held onto it for Keith and Keith passed on it…And I feel like you guys could really, really do this song, do a great job with this song.’”

He recalls him and his bandmates Gary LeVox and Joe Don Rooney seeing the chorus Jeffrey Steele had written and thinking it was a “no-brainer.” It turned out following their gut instinct paid off because “What Hurts The Most” went on to become their fifth No. 1 on the Billboard Hot Country Songs, their first Top 10 on the all-genre Billboard Hot 100, and a No. 1 on the Adult Contemporary charts. Additionally, it earned two GRAMMY nominations.

“Throughout our careers, we’d always been really good about not being precious about songs we had written, we’d always let the best song win,” DeMarcus continued. “And this song just stood out as one of those pieces of music that was so far above everything else we had had held at that point…it just felt like one of those moments we’d captured some lightning in a bottle.”

Had Urban decide to record it, the song could have had an entirely different sound and feel to it, but Rascal Flatts’ soaring harmonies and emotional delivery gave it the kind of powerful vulnerability that would resonate with millions.

The song appeared on the Me and My Gang album alongside other landmark tracks like “Stand,” the title track, their cover of “Life Is A Highway” and “My Wish.”

“It was another Jeffrey Steele song. He was on fire at that time. I remember every time he would do a demo session, people were chomping at the bit to listen to the demos and hear what songs and what genius he’d come up with,” DeMarcus shared. “And that song was very personal for him. And you could certainly hear it through the demo. When he sang and delivered the vocal, you could tell there was so much emotion behind it. And I think our job was to try to recapture some of that magic and some of that emotion in the vocal delivery of what he had because it was so magical and so special hearing him sing it.”

He admits it was a “tough job” to try and replicate that immense passion, raw emotion and vulnerability within the lyrics that were inspired by Steele’s love for his youngest daughter.

“It’s just a testament to Gary too and what an incredible singer he is and how he’s able to digest something and make it his own and turn it into something so powerful.”

“What Hurts The Most” marked the first single from heir 2006 album while “My Wish” served as the fourth single. As a whole, the project remains an iconic project in their career. It was named the best-selling album and the best-selling country album of 2006 and went 4x platinum.

DeMarcus went on to recall the moment he realized just how big of an impact this collection really had made in the music world at the time.

“The whole ‘Me and My Gang’ record is kind of our Joshua tree. I think all the stars aligned came together…At the risk of sounding egotistical, that record that year sold more records than any other record in the world, six and a half million records. And we were sitting at the Grammys, and I never will forget during commercial break, Gary leaned over to me and he said, ‘Hey cuz, look at the people that we’re sitting in the room with. There’s Beyonce, there’s Jay-Z, there’s this Lady Gaga, Elton John.’ And I was like, ‘Yeah, I can’t believe this, man. We’re sitting in the same room.’ And he goes, ‘Now think about this. We sold more records than anybody out here this year.’”

“And that’s one of those memories that chokes me up because when you dream about being an artist, you hope you make it to the Grammys, you hope you have a hit song, but that’s one of the memories that I’ll always share with Gary that was uniquely our own just between the two of us.”

It’s safe to say that Rascal Flatts’ musical journey only continued to climb and flourish from that moment. Even to this day, fans continue to flock to their shows, and sing along to the songs that cemented their place as one of the genre’s most powerful vocal groups.

Last year, they returned to the road with the Life is a Highway Tour and are set to reunite with their supporting acts Chris Lane and Lauren Alaina in 2026 for even more dates. Kicking off on January 15 in Raleigh, North Carolina, the tour will make stops in Nashville, Chicago, Tampa, and more before wrapping up on February 28 in Buffalo, New York.